1. having the most rocks or being the most rocky in terrain
Usage: superlative form of rocky
2. most unstable, difficult, or troubled
Usage: figurative use

Examples

• This is the rockiest trail in the entire mountain range.
• The rockiest part of the coastline is dangerous for boats.
• They chose the rockiest path up the cliff face.
• Their marriage went through its rockiest period last year.
• The company survived its rockiest financial quarter.
• The rockiest stretch of road required careful driving.